Fail Harder: How going Offline caused me to be late and created room for serendipity

Time for the end of week evaluation. In case you’re reading this with no clue what I’m talking about, check out last week’s post, Working Deep and Shallow for some context. The short version: in an experiment to optimize for, “Deep Work,” I restructured my schedule at work to see if I could be more productive.

On Day 1, I blocked off time on my calendar for Focus Time, I scheduled two 30 min blocks of email batch processing, I scheduled time for lunch, and I scheduled interruptible time for, “Shallow Work.” Day 1 mostly succeeded, except for the fact that everything went over and none of the times actually lined up. I got into the Flow and lost track of time and when I started doing email, I took an hour instead of 30 min.

The rest of the week led me down the treacherous slope of interruptions, email vortex, and urgency over proactivity. In short, I failed. But I learned some things along the way.

Thing 1: I’m too nice

If you don’t prioritize your own time over others people’s time, no one else will.

The difficulty with time management is that it’s always at the mercy of someone else. Or, at least it seems that way. I can set my schedule and try to do what I want to do, but other people are also doing the same. If they want to talk to me, they request a time that works for them (and hopefully works for me) but it’s their request on my time.

No one else is prioritizing your time.

Sure, everything will get done faster if we just talk in person. And if it’s something that needs to get done, then I want to prioritize that so that things keep moving forward. You might also hear: “I’m going to be on vacation next week and I’d really like to talk to you about a few things before I leave.” This is an even harder one to say no to. Especially if it’s someone that I really want to impress, or someone that I’m working with on something important.

What’s really tough is that everyone means well, unless you’re a taker, and then you just need to stay away. It’s easier to be accommodating than to say, “Can we meet after 3 pm when I’m free?” or “I’m heads-down on something important, would later today work?” Other people don’t arrange their schedules the way that I do, but if every productivity blog out there says the same things (Batch process email, you’re most productive in the morning, distractions and notifications are the killer of productivity, etc.) then why aren’t we all spending our mornings working?

Hmm. Why aren’t we spending our mornings to do our best work?

Thing 2: Work Culture determines a lot of defaults

I can’t control when other people’s meetings are scheduled. I can’t help that a review is scheduled for Friday mornings or the Leadership Team also meets in the morning. Granted, they aren’t all morning, but it either breaks up my morning so much that I can’t work before and afterwards or there are two of them back to back that literally take up all the time I’m in the office.

If I went to those two meetings alone, that leaves only three other mornings available. Let’s say I could actually get a good solid 2 hours of productive work on 3 mornings: that’s 6 hours a week. Not very much, really.

On top of all this, other teams have meetings in the afternoon. And if I plan my afternoons as interruptible time, they get interrupted by meetings.

I do have control over meetings I create, however. And I’ve been creating fewer and fewer of them. So, I’ll only create one when it has a purpose and is absolutely necessary. I wish everyone was more vigilant about meetings.

Thing 3: I should do more of the things I can control

At the same time, there is a delicate balance between going to a select few meetings and not going to enough meetings. At times, I’ve been called out for not attending something I should have been at. Being a manager, I have my directs go to more of the day to day meetings and I’m there for the big, important ones. Unless there is something else going on that’s equally as important that I have to be at. And then I have to make a call. Sometimes I make the wrong call, but it’s a call. And very often, no matter which I pick, someone will not be happy.

Thing 4: Going Offline was scary, amazing, and terrible all at once

Going Offline was amazing. Like seriously it was. My absolute favorite day in the entire week is Saturday. Not because I don’t work, but because I spend 3–4 hours reading alone in my reading room before my partner wakes up. Without technology. I read fiction, non-fiction, poetry, and I look at Art, Design, and Architecture books. It’s the most fulfilling time of my entire week. What if work could be more like that? Not distracted by email. Working productively on something I’m passionate about. I actually read “Work books” during this time as well. And I’m completely happy doing it.

Going Offline was amazing, but not because of what I did; Going offline was amazing because of what I didn’t do.

I didn’t stress out about that project at work. I didn’t get distracted by some social media notification and then go into the black hole. I didn’t start surfing the news. I didn’t watch a silly cat video or anything on YouTube. I enjoy all of these things (except the stress part). And it was freeing to not do any of them.

So much of my life is based in technology, it’s just really wonderful to have times when I’m not using any. I work in tech. I consume music, podcasts, and learn languages in the car to and from work. I watch tv shows on Netflix when I get home (Trashy reality tv shows, to be more specific). That’s why Saturdays are so great. I can curl up with a book in my favorite room and hear the sound of the pages as I turn them. I can smell the smell of ink on pages. Some books really smell wonderful.

Come to think of it, I should really call my reading room, my analog room. The other activity I do in the reading room is listen to vinyl. I actually purchase vinyl of my favorite albums so that I can listen to them in the best possible way: with a nice, beautifully analog sound. I also have my Moog analog synthesizer and my Moog Semi-Modular analog synthesizer in this room. It totally fits. The books are in the library, just across the hall.

The only thing terrible about going offline was that I missed things. Like, I missed some important things. I missed a meeting that was rather important and I looked pretty bad for being 20 min late. I felt super bad too. Everyone was waiting for me and I was late… but the reason brings me to my final point.

Thing 5: Serendipity

  • I was at lunch and joined a friend I hadn’t seen in a while. We talked about how we were doing, what we were working on, my experiment that week, and have a wonderful connection.
  • Another day at lunch, I joined a friend and then made a new friend who he was sitting with.
  • I happened to be at my desk when someone walked by obviously upset. I had the time and the availability to be there for them.
  • I caught up with a colleague and found out that we were working on similar things and decided to join forces on a project.

All of these would not have happened had I been on my phone, checking my email. Or booked in meetings all day (and going to them).

Where do we go from here?

  1. Be vigilant about your time
  2. Accept fewer meetings
  3. Create fewer meetings
  4. Save your mornings for doing your best work
  5. Reduce your time “doing email”
  6. Batch process responses to twice a day
  7. Click on that “Work offline” button more often
  8. Make room for serendipity



Co-Founder & CEO @, composer, reader, and thinker.

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